| 7. Journée | 03.08.2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 |  |
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| 9. Journée | 17.08.2008 | Provincial Osorno (old) | - | Cobresal | 0:3 | ||||
| 10. Journée | 23.08.2008 | Audax Italiano | - | Provincial Osorno (old) | 1:2 | ||||
| 11. Journée | 31.08.2008 | Provincial Osorno (old) | - | Universidad de Chile | 1:2 | ||||
| 17. Journée | 25.10.2008 | Palestino | - | Provincial Osorno (old) | 1:0 | ||||
| 19. Journée | 09.11.2008 | Provincial Osorno (old) | - | Unión Española | 1:2 |
Chili